Lindsay Lohan, one of the most controversial young celebrities of her time has recently been asked by Playboy's Hugh Hefner to re-shoot a spread set with a Marilyn Monroe-like concept.

The young singer-actress was attending the photo set while meeting up her appointed court dates. Hefner did not like much the initial results and hence it was extended up to the weekend. According to the big boss, the original shots done looked somehow like Kate Moss and not of Monroe appeal.

Lindsay Lohan or better known by the press as LiLo started as a child actress who did well in the movies and even in the music industry as a singer. She is a designer of clothes and also a well known socialite because of the popularity of both her parents as well. She got high praise and recognition for her role in the 'Mean Girls' movie but no one ever expected she would end up, somehow being one, in real life.

Let us take a look back at six of her most controversial photo shoots she has done for prominent magazine covers through the years. What do you expect of the upcoming Playboy cover?

Check out the slideshow of the sexy covers

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Court Lindsay Lohan